My Mission

In this case study, I’ll show you how I coached a large, over-burdened engineering organization to take ownership of and improve their leadership, teamwork, process, and operations.

In this case study, I’ll show you how I coached a fast-growing marketing automation platform to overcome three key existential crises at once.

At the end of every year, I spend the holidays reflecting on my year, what went well, what didn’t go well, and what I can do in the next year to be a better version of myself. I take all of my coaching clients through this process as well. This year, I decided to open-source my Personal Retrospective Guide so that everyone can benefit.

I’ve been leading and coaching software development teams for fifteen years, and there is one problem that has surfaced in some form in every single team I’ve ever worked with. The problem begins when the Product Owner asks the engineers to work on a vague story with very little context and no acceptance criteria. This is called Requirements Churn.

In agile development, we strive to maximize efficient output while maintaining a sustainable pace. It’s the team’s responsibility to constantly assess their capacity, take on work up to, but not exceeding their capacity, and consistently invest in continuous improvement to increase capacity over time.

If you’ve ever managed or built a product, you know that gathering and analyzing customer feedback is hard.

It’s time-consuming; you have to spend hours prospecting customers and following up to schedule interviews or collect surveys. More often than not, the responses received aren’t specific enough or lack the context necessary for in-depth analysis. Not only do you have to collect, clean, and organize your data, but you also need it to be relevant and meaningful. What if I told you that there was a better solution for this?

There’s nothing more inefficient than building the wrong things, so how do you know if your product features are going to make an impact? I’ve covered the Pirate Metrics framework as a way to evaluate and prioritize features from a business perspective, but what we really want to know is the impact a feature makes from the user’s perspective. For that, we need a slightly different model.

It’s hard to develop a really good elevator pitch. You’ve probably been in this situation. You’re at a networking event, and someone asks you what your product does. Maybe you’ve been trying to clearly convey to potential investors how your product solves a real problem and is better than the competitors.

I’ve been there myself. I was running a Lean Canvas workshop a few years ago when the perfect analogy came to me. You know who absolutely nails the sales message in a short amount of time?

Infomercials.

My entire career has been focused on building complex systems and executing with ruthless efficiency. As CTO at my last company, I earned the nickname “The Executioner”, because of my relentless drive to Get. Shit. Done.

But it wasn’t enough…

In order to build a product your customers love, you need to get inside their heads. It’s not enough to understand what they do, you must understand why. This requires you to interact with your customers on a deep, personal level and gather data from various perspectives. Early on, you should spend a significant proportion of your time gathering user feedback, and as the company grows, you must invest in developing the systems and processes to make it a part of the DNA of your company.

I wasn’t sleeping, I didn’t have time to exercise or eat well, and I started drinking more to cope. I was fighting with my CEO and my wife on a daily basis. I would wake up at 5am with a rush of panic because I knew I was already behind and there was nothing I could do. I accepted the fact that every single day I was going to fail my family, my company, and myself.

I’m completely, philosophically opposed to the Gary V school of thought that success is created by sheer force of will, that grinding 16 hours a day every day will make you successful. Yes, there are going to be crunch periods, and yes, building a successful business takes a lot of work, but this #Hustle culture creates the mindset that you, the founder, are like Atlas, with the weight of the world on your shoulders. I’m here to tell you that this approach is not only wrong, it’s unhealthy, unsustainable, and unscalable.